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Volume 69 
Part 12 
Pages o1851-o1852  
December 2013  

Received 16 November 2013
Accepted 22 November 2013
Online 30 November 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.005 Å
R = 0.044
wR = 0.113
Data-to-parameter ratio = 14.9
Details
Open access

2-[(E)-2-(4-Hy­droxy-3-meth­oxy­phen­yl)ethen­yl]-1-methylpyridinium 4-bromo­benzene­sulfonate monohydrate

aDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand,bFaculty of Traditional Thai Medicine, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: suchada.c@psu.ac.th

The title salt crystallized as the monohydrate C15H16NO2+·C6H4BrSO3-·H2O. The cation exists in an E conformation with respect to the ethynyl bond and is essentially planar, with a dihedral angle of 6.52 (14)° between the pyridinium and the benzene rings. The hy­droxy and meth­oxy substituents are coplanar with the benzene ring to which they are attached, with an r.m.s. deviation of 0.0116 (3) Å for the nine non-H atoms [Cmeth­yl-O-C-C torsion angle = -0.8 (4)°]. In the crystal, the cations and anions are stacked by [pi]-[pi] inter­actions, with centroid-centroid distances of 3.7818 (19) and 3.9004 (17) Å. The cations, anions and water mol­ecules are linked by O-H...O hydrogen bonds and weak C-H...O inter­actions, forming a three-dimensional network.

Related literature

For applications of stilbene derivatives, see: Chanawanno et al. (2010[Chanawanno, K., Chantrapromma, S., Anantapong, T., Kanjana-Opas, A. & Fun, H.-K. (2010). Eur. J. Med. Chem. 45, 4199-4208.]); Frombaum et al. (2012[Frombaum, M., Le Clanche, S., Bonnefont-Rousselot, D. & Borderie, D. (2012). Biochimie, 94, 269-276.]); Hussain et al. (2009[Hussain, M., Khan, K. M., Ali, S. I., Parveen, R. & Shim, W. S. (2009). Fibers Polym. 10, 407-412.]); Jindawong et al. (2005[Jindawong, B., Chantrapromma, S., Fun, H.-K., Yu, X.-L. & Karalai, C. (2005). Acta Cryst. E61, o1340-o1342.]); Kobkeatthawin et al. (2009[Kobkeatthawin, T., Suwunwong, T., Chantrapromma, S. & Fun, H.-K. (2009). Acta Cryst. E65, o76-o77.]); Li et al. (2013[Li, X., Lu, H., He, D., Luo, C. & Huang, J. (2013). J. Fluoresc. 23, 1039-1044.]); Ruanwas et al. (2010[Ruanwas, P., Kobkeatthawin, T., Chantrapromma, S., Fun, H.-K., Philip, R., Smijesh, N., Padakid, M. & Isloor, A. M. (2010). Synth. Met. 160, 819-824.]). For related structures, see, Chanawanno et al. (2009[Chanawanno, K., Chantrapromma, S. & Fun, H.-K. (2009). X-ray Struct. Anal. Online, 25, 127-128.]); Chantrapromma et al. (2013[Chantrapromma, S., Ruanwas, P., Jindawong, B. & Fun, H.-K. (2013). Acta Cryst. E69, o1623-o1624.]); Fun et al. (2011[Fun, H. K., Chantrapromma, S. & Jansrisewangwong, P. (2011). Acta Cryst. E67, o105-o106.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]) and for hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer, (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C15H16NO2+·C6H4BrO3S-·H2O

  • Mr = 496.37

  • Triclinic, [P \overline 1]

  • a = 9.8201 (13) Å

  • b = 10.3315 (14) Å

  • c = 12.4914 (17) Å

  • [alpha] = 99.898 (2)°

  • [beta] = 111.134 (2)°

  • [gamma] = 107.042 (2)°

  • V = 1074.1 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 2.05 mm-1

  • T = 100 K

  • 0.59 × 0.15 × 0.14 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.378, Tmax = 0.768

  • 11172 measured reflections

  • 4186 independent reflections

  • 3356 reflections with I > 2[sigma](I)

  • Rint = 0.021

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.113

  • S = 1.05

  • 4186 reflections

  • 281 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.93 e Å-3

  • [Delta][rho]min = -0.94 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H1O2...O1Wi 0.82 1.88 2.685 (4) 169
O1W-H2W1...O4ii 0.81 (5) 2.03 (5) 2.834 (4) 172 (5)
O1W-H1W1...O3iii 0.81 (4) 1.99 (5) 2.793 (5) 173 (5)
C1-H1A...O5iv 0.93 2.57 3.491 (4) 170
C2-H2A...O1v 0.93 2.51 3.440 (4) 176
C2-H2A...O2v 0.93 2.60 3.183 (4) 121
C3-H3A...O2v 0.93 2.54 3.160 (4) 124
C14-H14A...O4iv 0.96 2.54 3.448 (5) 158
Symmetry codes: (i) x-1, y, z-1; (ii) x-1, y, z; (iii) -x+1, -y, -z+1; (iv) -x+2, -y+1, -z+1; (v) x+1, y+1, z+1.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]), Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5370 ).


Acknowledgements

The authors thank Prince of Songkla University for generous support and also thank the Universiti Sains Malaysia for the APEX DE2012 grant No. 1002/PFIZIK/910323.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chanawanno, K., Chantrapromma, S., Anantapong, T., Kanjana-Opas, A. & Fun, H.-K. (2010). Eur. J. Med. Chem. 45, 4199-4208.  [Web of Science] [CSD] [CrossRef] [ChemPort] [PubMed]
Chanawanno, K., Chantrapromma, S. & Fun, H.-K. (2009). X-ray Struct. Anal. Online, 25, 127-128.  [CrossRef] [ChemPort]
Chantrapromma, S., Ruanwas, P., Jindawong, B. & Fun, H.-K. (2013). Acta Cryst. E69, o1623-o1624.  [CrossRef] [ChemPort] [IUCr Journals]
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [Web of Science] [IUCr Journals]
Frombaum, M., Le Clanche, S., Bonnefont-Rousselot, D. & Borderie, D. (2012). Biochimie, 94, 269-276.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Fun, H. K., Chantrapromma, S. & Jansrisewangwong, P. (2011). Acta Cryst. E67, o105-o106.  [CrossRef] [ChemPort] [IUCr Journals]
Hussain, M., Khan, K. M., Ali, S. I., Parveen, R. & Shim, W. S. (2009). Fibers Polym. 10, 407-412.  [CrossRef] [ChemPort]
Jindawong, B., Chantrapromma, S., Fun, H.-K., Yu, X.-L. & Karalai, C. (2005). Acta Cryst. E61, o1340-o1342.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Kobkeatthawin, T., Suwunwong, T., Chantrapromma, S. & Fun, H.-K. (2009). Acta Cryst. E65, o76-o77.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Li, X., Lu, H., He, D., Luo, C. & Huang, J. (2013). J. Fluoresc. 23, 1039-1044.  [CrossRef] [ChemPort] [PubMed]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Ruanwas, P., Kobkeatthawin, T., Chantrapromma, S., Fun, H.-K., Philip, R., Smijesh, N., Padakid, M. & Isloor, A. M. (2010). Synth. Met. 160, 819-824.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1851-o1852   [ doi:10.1107/S1600536813031917 ]

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